Things to do in
Gloucester, Massachusetts

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Our most recommended things to do in Gloucester, Massachusetts

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

1. Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Start a journey through the less-explored part of Massachusetts. Discover scenic beaches and historic towns as you drive, listen to the stories provided on the tour app, and stop for photos throughout the tour whenever you like. Begin the tour in Gloucester. When you drive, the app will provide instructions on how to use it. Then, head toward State Fort Park where you will hear about the Tablet Rock. From there, move on to the Fisherman’s Wives memorial and learn about its significance. Proceed on to the Fisherman’s Memorial over the Blynnman Canal Bridge before stopping for a stroll at Gloucester HarborWalk. Enjoy the view of the sea and pay a visit to the Maritime Museum, if you want. Next, see whales from the Cape Ann Whale watchpoint before discovering one of the oldest colonies in the U.S., Rocky Neck Art Colony. Make further stops at Niles Beach, Beauport Mansion, Eastern Point Lighthouse, Good Harbor Beach, and Pebble Beach. After Pebble Beach, you will be approaching Rockport before beginning the return journey to Gloucester. This part of the tour has some trivia and interesting spots to keep you engaged. On the way back, pass Halibut Point State Park and Harvey Reservation. If you want, you can take a break at Plum Cove Beach after the park. The tour then concludes at the Goose Cove reservation.

Boston, Harvard & Cape Cod Self-Guided Audio/Driving Tour

2. Boston, Harvard & Cape Cod Self-Guided Audio/Driving Tour

Start in the city of Boston and walk in the footsteps of Revolutionary War heroes. Hear the story of Paul Revere’s Midnight Ride and relive the fight for American Independence with a self-guided walking tour of Boston’s Freedom Trail. Immerse yourself in the stories of the American Revolution, the Boston Tea Party, and the Sons of Liberty as you stroll along Boston’s scenic Harborwalk. Uncover Boston's historic and storied past while enjoying its beautiful harbor views between South Station and Long Wharf. Then, travel to the city of Cambridge outside Boston and explore the heart of Harvard University's campus at Harvard Square. Use the app to take a self-guided walking tour that covers must-see campus sights like the John Harvard Statue, Widener Library, and former dorm rooms of famous alumni like Bill Gates, Mark Zuckerberg, Natalie Portman, and more. Next, discover Cape Ann with a self-guided driving tour along the scenic waterfront. Enjoy the vistas, beaches, and natural beauty of the New England coastline at your own pace. Visit the famous Fisherman's Memorial, beautiful Beauport, all while diving into the stories of Massachusetts of days past. Continue to Cape Cod and see its quintessential lighthouses and sandy beaches. As you drive, learn more about the Cape’s seafaring traditions, Pilgrim history, and miles of beautiful beaches. From Barnstable to Provincetown, visit Nauset Lighthouse, First Encounter Beach, Marconi Station, and more.

Boston: American Revolution Walking & Driving Private Tour

3. Boston: American Revolution Walking & Driving Private Tour

Discover the history of the American Revolution on a private self-guided walking and driving tour. Explore the freedom trail of Boston, Harborwalk, and more at your own pace with an audio guide. You will receive the download instructions after booking. Download the app and start the tour with your mobile phone as your guide. You will hear about the history, and the battles fought on the grounds.  Walk in the shoes of the Founding Fathers on the Freedom Trail and hear how the first sparks of revolution flew in Boston. Learn about the Sons of Liberty and uncover the truth about misunderstood events like the Boston Massacre. Next, reach Boston’s Harborwalk and revisit the fiery lead-up to the American Declaration of Independence. Stroll along the waterside and know about the dramatic protest called the Boston Tea Party and get a chance to visit the site. Afterward, head to the famous towns Lexington and Concord. Follow the route of an impossible battle between the American military and the British redcoats. Find out how the Americans turned the tide, and hear what it all meant in the fight for American independence. Then head to Valley Forge, where General George Washington faced some of his toughest challenges. Here, you will explore the remains of Washington’s 18th-century camp and hear the harrowing tale of how frigid temperatures, starvation, and desertion nearly pulled the American army apart. Finally, you will tour Philadelphia, where the Declaration of Independence was first signed. Hear stories about Ben Franklin and the other revolutionaries who called this city home. See the iconic landmarks like the famous Liberty Bell and Elfreth’s Alley, maintained just as it was in the 1700s.

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What people are saying about Gloucester, Massachusetts

Overall rating

4.7 / 5

based on 3 reviews

Amazing information, great price! I love the flexibility to start, stop, not go in order. Very nice experience and really enjoyed it.